Chen Jia-run
2009
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Journal
Journal of Shenyang Pharmaceutical University
Abstract
Objective To synthesize 2-Phenyl-1-butanol and 2-dimethylamino-2-phenylbutanenitrile,the key intermediates for the synthesis of trimebutine.Methods 2-Phenylacetonitrile was alkylated with bromoethane to prepare 2-phenylbutanenitrile,which was hydrolyzed to give 2-phenylbutanoic acid,and then the intermediate was reduced with NaBH4-I2 system to give 2-phenyl-1-butanol.The 2-bromo-2-phenylacetonitrile was obtained by bromination of 2-phenylacetonitrile with NBS,followed by amination with dimethylamine to afford 2-dimethylamino-2-phenylacetonitrile,finally,the intermediate was alkylated with bromoethane to give 2-dimethylamino-2-phenylbutanenitrile.Results 2-Phenyl-1-butanol and 2-dimethylamino-2-phenylbutanenitrile were synthesized with total yields of 51% and 59.4% respectively,and the structures of the target compounds were identified by 1H-NMR and ESI-MS.Conclusions Two efficient synthetic routes are developed for the syntheses of 2-phenyl-1-butanol and 2-dimethylamino-2-phenylbutanenitrile separately.